Securinine (C13H15NO2; mw 217.2637; also known as CHEMBL303062; Securinin; Securinan-11-one; 5610-40-2; Securinine, (−)-; UNII-G4VS580P5E; NSC107413, as well as stereoisomers virosecurinine and allosecurinine) is a small molecule with the recognized two-dimensional structure:

Securinine is a plant-derived alkaloid that has previously demonstrated efficacy for neurological related diseases. An unexpected rearranged derivative, norsecurinine, has recently been reported (Li et al., Tetrahedron 2012, 68, 3972-3979):
As well as a brominated derivative:

Securinine is documented as an effective GABAA receptor antagonist with otherwise very low cellular toxicity (Beutler et al., Brain Res 330(1); 135-140, 1985; Lubick et al., J Leukoc Biol. 2007 November; 82(5):1062-9). Securinine has further been identified to induce apoptosis of promyelocytic leukemia cells and colon cancer cells at high doses and to induce monocytic differentiation of a wide range of myeloid leukemia cell lines as well as primary leukemic patient samples at low doses (Rana et al., 2010, The FASEB Journal, 24(6) 2126-2134; Dong et al., Zhongguo yao li xue bao=Acta pharmacologica Sinica 20.3 (1999): 267-270; Gupta et al., PLoS ONE 6(6): e21203. doi:10.1371/journal.pone.0021203, 2011). Securinine has also been found to lead to cell killing of other cancer cell types such as breast cancer. (Li et al., Pharmazie 69: 217-23 (2014). Additional studies have focused on adapted structures derived from synthesizing the securinine molecule and noted its potential for a wide variety of infectious diseases such as parasitic disease. For example, the differences in activity on toxoplasma growth between the various derivatives (Holmes et al. Experimental parasitology 127.2 (2011): 370-375) was investigated. It also has activity against fungi (Sahni et al., Mycobiology 33.2 (2005): 97-103). Securinine has also been found to have activity in modulating infectious diseases through its ability to enhance the host immune response. For example, it enhances the ability of macrophages to clear a bacterial infection. (Lubick et al., Journal of leukocyte biology 82.5 (2007): 1062-1069).
Others have identified a natural reductase that reduces the γ,δ double bond of securinine and presented various derivatives of the reduced securinine (with functional groups affixed at C15) that also alter myeloid cell activity (Guan et al., Biotechnology letters 27.16 (2005): 1189-1193; US Published Patent Application 20140018383). Given the apparent diverse cellular activity offered by securinine as a backbone, investigations were aimed at identifying new cellular targets that analogs may interact with.